filup501,
Depends on the crew and your ability to communicate in such a way that they don't kill you. A little bit of pre-training goes a long way. It also depends on the boat of course. Most charterboats are set up well for short handing/singlehanding.
The bottom
line is it all comes down to attitude and the fact that with the sails stowed it's just a powerboat. The BVI is a good place to learn.